Recyclable Palladium-Catalyzed Carbonylative Cyclization of Trifluoroacetimidoyl Chlorides with Nitro Compounds Towards 2-(Trifluoromethyl)quinazolin-4(3H)-ones
摘要
A new mesoporous SBA-15-anchored Schiff base and phosphine mixed bidentate palladium(II) complex [SBA-15-N, P-PdCl2] was prepared via immobilization of 3- aminopropyltriethoxysilane on SBA-15, followed by condensation with 2–(diphenylphosphino)benzaldehyde and then coordination with PdCl2. With the use of 5 mol% of SBA15-N, P-PdCl2 as catalyst, the carbonylative cyclization between trifluoroacetimidoyl chlorides and nitro compounds proceeds smoothly in 1,4-dioxane at 120 °C with Na2CO3 (2 equiv.) as base by using Mo(CO)6 (2 equiv.) as both a solid CO source and a reductant, yielding a variety of 2-(trifluoromethyl)quinazolin-4(3H)-ones in 68–94% yields. The SBA-15-N, P-PdCl2 complex can be easily separated by a simple centrifugation process and recycled more than 8 cycles without a remarkable loss of activity. The current protocol not only solves the basic problem of expensive palladium catalyst recovery and reuse, but also prevents palladium contamination in the final product.
Graphical Abstract